89095
(R)-Tetrahydrofurfuryl alcohol
≥98.0% (sum of enantiomers, GC)
Synonym(s):
(R)-Tetrahydrofuran-2-methanol
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About This Item
Empirical Formula (Hill Notation):
C5H10O2
CAS Number:
Molecular Weight:
102.13
Beilstein:
79846
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Assay
≥98.0% (sum of enantiomers, GC)
form
liquid
optical purity
enantiomeric ratio: ≥97:3% (GC)
bp
178 °C (lit.)
density
1.054 g/mL at 20 °C (lit.)
functional group
ether
hydroxyl
SMILES string
OC[C@H]1CCCO1
InChI
1S/C5H10O2/c6-4-5-2-1-3-7-5/h5-6H,1-4H2/t5-/m1/s1
InChI key
BSYVTEYKTMYBMK-RXMQYKEDSA-N
Application
(R)-Tetrahydrofurfuryl alcohol can be used:
- To prepare (R)-tetrahydrofurfuryl aldehyde, which is employed as a building block to synthesize a fragment of pectenotoxin-4.[1]
- As a starting material to synthesize naftidrofuryl isomers, used as potent 5-hydroxytryptamine 2A receptor antagonists.[2]
- As a building block for the preparation of (S)-2-tetrahydrofuran methyl ether 6-fluorophenyl ether analog, as an IGF-1R inhibitor.[3]
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Rhodium-catalysed vinyl 1, 4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4
Richardson MSW, et al.
Chemical Science, 10(25), 6336-6340 (2019)
Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor
Hao J, et al.
Bioorganic & Medicinal Chemistry Letters, 22(10), 3441-3444 (2012)
Optimisation of a 5-[3-phenyl-(2-cyclic-ether)-methyl-ether]-4-aminopyrrolopyrimidine series of IGF-1R inhibitors
Fairhurst RA, et al.
Bioorganic & medicinal chemistry letters, 26(8), 2057-2064 (2016)
T Schräder et al.
Journal of bacteriology, 183(24), 7408-7411 (2001-11-22)
Different aldehyde dehydrogenases (AlDHs) were formed during growth of Ralstonia eutropha Bo on tetrahydrofurfuryl alcohol (THFA). One of these enzymes, AlDH 4, was purified and characterized as a homodimer containing no prosthetic groups, showing a strong substrate inhibition, and having
G Zarnt et al.
Journal of bacteriology, 183(6), 1954-1960 (2001-02-27)
The quinohemoprotein tetrahydrofurfuryl alcohol dehydrogenase (THFA-DH) from Ralstonia eutropha strain Bo was investigated for its catalytic properties. The apparent k(cat)/K(m) and K(i) values for several substrates were determined using ferricyanide as an artificial electron acceptor. The highest catalytic efficiency was
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